3-methylazulene-1-carboxylic acid | 58313-03-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 3-methylazulene-1-carboxylic acid
• 英文别名: 3-methyl-1-azulenecarboxylic acid；3-Methyl azulene-1-carboxylic acid
• CAS: 58313-03-4
• 化学式: C₁₂H₁₀O₂
• 分子量: 186.21
• InChiKey: FZZVRWQKRNCMBP-UHFFFAOYSA-N

物化性质

• 熔点：
  196 °C
• 沸点：
  376.9±11.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methylazulene-1-carboxylic acid 在 三氯乙酸 作用下， 以 苯 为溶剂， 反应 2.0h， 以95%的产率得到1-甲基薁
  参考文献：
  名称：

  A Versatile Synthetic Method of 1-Alkylazulenes and Azulene by the Reactions of 3-Methoxycarbonyl-2H-cyclohepta[b]furan-2-one within situGenerated Enamines

  摘要：

  甲基3-烷基莫I-1-羧酸酯通过3-甲氧羰基-2H-环庚[b]呋喃-2-酮与现场生成的吗啉烯胺醛反应以高产率合成。用100%磷酸处理这些酯，可以以优异的产率得到1-烷基莫I。通过这种方法的改进，以及甲基莫I-1-羧酸酯，莫I也在良好的产率下合成。

  DOI：

  10.1246/bcsj.66.892
• 作为产物：
  描述：

  methyl 3-methylazulene-1-carboxylate 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以100%的产率得到3-methylazulene-1-carboxylic acid
  参考文献：
  名称：

  A Versatile Synthetic Method of 1-Alkylazulenes and Azulene by the Reactions of 3-Methoxycarbonyl-2H-cyclohepta[b]furan-2-one within situGenerated Enamines

  摘要：

  甲基3-烷基莫I-1-羧酸酯通过3-甲氧羰基-2H-环庚[b]呋喃-2-酮与现场生成的吗啉烯胺醛反应以高产率合成。用100%磷酸处理这些酯，可以以优异的产率得到1-烷基莫I。通过这种方法的改进，以及甲基莫I-1-羧酸酯，莫I也在良好的产率下合成。

  DOI：

  10.1246/bcsj.66.892

文献信息

• Synthesis of Azulenopyridinones through Palladium‐Catalyzed Oxidative [4+2] Cyclization Reactions of <i>N</i> ‐Methoxyazulene‐1‐ and 2‐carboxamides with Alkynes
  作者：Gi Uk Han、Jeong‐Yu Son、Dahee Park、Hyeonsik Eom、Kyungsup Lee、Hee Chan Noh、Kooyeon Lee、Phil Ho Lee

  DOI：10.1002/adsc.202000587

  日期：2020.11.4

  oxidative [4+2] cyclization reactions were developed from the C−H activation reaction of N‐methoxyazulene‐1‐ and 2‐carboxamides with symmetrical and unsymmetrical alkynes under a molecular oxygen atmosphere, producing azulenopyridinone derivatives with novel azulene skeletons in good to excellent yields with a wide substrate scope and excellent functional group tolerance.

  钯催化的氧化[4 + 2]环化反应是由N-甲氧基azulene-1和2-羧酰胺与对称和不对称炔烃在分子氧气氛下的C–H活化反应发展而来的，在此过程中生成具有新颖氮杂环骨架的氮杂吡啶并酮衍生物具有良好的优异产率，具有广泛的底物范围和出色的官能团耐受性。
• Iridium(III)-Catalyzed Sequential C(2)-Arylation and Intramolecular C–O Bond Formation from Azulenecarboxylic Acids and Diaryliodonium Salts Access to Azulenofuranones
  作者：Chanyoung Maeng、Hyung Jin Seo、Haneal Jeong、Kyungsup Lee、Hee Chan Noh、Phil Ho Lee

  DOI：10.1021/acs.orglett.0c02607

  日期：2020.9.18

  herein is the iridium-catalyzed sequential C(2)-arylation reaction and intramolecular C–O bond formation from azulenecarboxylic acids and diaryliodonium salts, leading to the formation of 3-arylazulenofuranones. The sequential reaction proceeded smoothly through generation of 2-arylazulene-1-carboxylic acids derived from the iridium-catalyzed regioselective C(2)-arylation reaction without the decarboxylation

  本文描述的是铱催化的连续C（2）-芳基化反应以及由氮杂羧酸和二芳基碘鎓盐形成的分子内C-O键，从而导致3-芳基氮杂呋喃酮的形成。顺次反应通过产生自铱催化的区域选择性C（2）-芳基化反应而没有脱羧反应的2-芳基氮杂-1-羧酸而顺利进行。
• Synthesis of azulenolactones through sequential C(2)‐bromoarylation and intramolecular CO bond formation from azulene‐1‐carboxylic acids and di(2‐bromoaryl)iodonium salts in <scp>one pot</scp>
  作者：Chanyoung Maeng、Phil Ho Lee

  DOI：10.1002/bkcs.12503

  日期：2022.4

  C(2)-bromoarylation reaction and intramolecular CO bond formation from azulene-1-carboxylic acids and di(2-bromoaryl)iodonium salts produced azulenolactones in one pot. The sequential reaction proceeded smoothly through the copper(I)-mediated cyclization of 2-(2-bromoaryl)azulene-1-carboxylic acids derived from the regioselective iridium(III)-catalyzed C(2)-bromoarylation reaction without decarboxylation

  连续的 C(2)-溴芳基化反应和 azulene -1-羧酸和二(2-溴芳基)碘鎓盐的分子内 C O 键形成在一锅中产生 azulenolactones 。顺序反应通过铜(I) 介导的2-(2-溴芳基)azulene-1-羧酸环化顺利进行，该环化来源于区域选择性铱(III) 催化的C(2)-溴芳基化反应，无需脱羧。
• Certain heterocyclic N-substituted carboxamides
  申请人：Beecham Group p.l.c.

  公开号：US04882327A1

  公开（公告）日：1989-11-21

  Compounds of formula (I), or a pharmaceutically acceptable salt thereof: Y-CO-L-Z (I) wherein L is NH or O; Y is a group of formula (a), (b) or (c): ##STR1## wherein R.sub.1 and R.sub.2, R.sub.5 and R.sub.6, R.sub.9 and R.sub.10, are independently selected from hydrogen or halogen; X is N or CR.sub.3 wherein R.sub.3 is hydrogen or C.sub.1-6 alkoxy; R.sub.4 is hydrogen, halogen, CH.sub.3, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkylsulphinyl, C.sub.1-7 acyl, cyano, C.sub.1-6 alkoxycarbonyl, C.sub.1-7 acylamino, hydroxy, nitro or amino, aminocarbonyl, or aminosulphonyl, optionally N-substituted by one or two groups selected from C.sub.1-6 alkyl, C.sub.3-8 cycloalkyl, and C.sub.3-8 cycloalkyl C.sub.1-4 alkyl or disubstituted by C.sub.4 or C.sub.5 polymethylene; phenyl or phenyl C.sub.1-4 alkyl group optionally substituted in the phenyl ring by one or two of halogen, C.sub.1-6 alkoxy or C.sub.1-6 alkyl groups; one of R.sub.7 and R.sub.8 is C.sub.1-6 alkyl and the other is C.sub.1-6 alkyl, phenyl or phenyl C.sub.1-4 alkyl optionally substituted in either phenyl ring by one or two of C.sub.1-6 alkoxy or halogen; or R.sub.7 and R.sub.8 together are C.sub.2-6 polymethylene or C.sub.2-5 polymethylene interrupted by an -O- linkage; R.sub.11 is hydrogen or C.sub.1-6 alkoxy; R.sub.12 is hydrogen, halogen, CF.sub.3, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkylsulphinyl, C.sub.1-7 acyl, cyano, C.sub.1-6 alkoxycarbonyl, C.sub.1-7 acylamino, hydroxy, nitro or amino, aminocarbonyl, or aminosulphonyl, optionally N-substituted by one or two groups selected from C.sub.1-6 alkyl, C.sub.3-8 cycloalkyl, and C.sub.3-8 cycloalkyl C.sub.1-4 alkyl or disubstituted by C.sub.4 or C.sub.5 polymethylene; phenyl or phenyl C.sub.1-4 alkyl optionally substituted in either phenyl ring by one or two of halogen, C.sub.1-6 alkoxy or C.sub.1-6 alkyl groups; Z is a group of formula (d), (e) or (f): ##STR2## wherein n is 2 or 3; p is 1 or 2; q is 1 to 3; r is 1 to 3; and R.sub.13 and R.sub.14 is C.sub.1-4 alkyl; having 5-HT.sub.3 receptor antagonist activity, a process for their preparation and their use as pharmaceuticals.

  公式（I）的化合物或其药学上可接受的盐：Y-CO-L-Z（I），其中L为NH或O；Y是公式（a），（b）或（c）的基团：##STR1##其中R.sub.1和R.sub.2，R.sub.5和R.sub.6，R.sub.9和R.sub.10，独立地选择氢或卤素；X为N或CR.sub.3，其中R.sub.3为氢或C.sub.1-6烷氧基；R.sub.4为氢，卤素，CH.sub.3，C.sub.1-6烷基，C.sub.1-6烷氧基，C.sub.1-6烷基硫醇基，C.sub.1-6烷基磺酰基，C.sub.1-6烷基亚磺酰基，C.sub.1-7酰基，氰基，C.sub.1-6烷氧羰基，C.sub.1-7酰胺基，羟基，硝基或氨基，氨基羰基或氨基磺酰基，可选择由C.sub.1-6烷基，C.sub.3-8环烷基和C.sub.3-8环烷基C.sub.1-4烷基中的一个或两个基团N-取代，或者由C.sub.4或C.sub.5聚亚甲基二取代的苯基或苯基C.sub.1-4烷基基团；苯基或苯基C.sub.1-4烷基基团，可选择在苯环上用一个或两个卤素，C.sub.1-6烷氧基或C.sub.1-6烷基基团取代；R.sub.7和R.sub.8中的一个是C.sub.1-6烷基，另一个是C.sub.1-6烷基，苯基或苯基C.sub.1-4烷基，在任一苯环上可选择用一个或两个C.sub.1-6烷氧基或卤素取代；或者R.sub.7和R.sub.8在一起是C.sub.2-6聚亚甲基或由-O-连接中断的C.sub.2-5聚亚甲基；R.sub.11为氢或C.sub.1-6烷氧基；R.sub.12为氢，卤素，CF.sub.3，C.sub.1-6烷基，C.sub.1-6烷氧基，C.sub.1-6烷基硫醇基，C.sub.1-6烷基磺酰基，C.sub.1-6烷基亚磺酰基，C.sub.1-7酰基，氰基，C.sub.1-6烷氧羰基，C.sub.1-7酰胺基，羟基，硝基或氨基，氨基羰基或氨基磺酰基，可选择由C.sub.1-6烷基，C.sub.3-8环烷基和C.sub.3-8环烷基C.sub.1-4烷基中的一个或两个基团N-取代，或者由C.sub.4或C.sub.5聚亚甲基二取代的苯基或苯基C.sub.1-4烷基基团；苯基或苯基C.sub.1-4烷基基团，可选择在苯环上用一个或两个卤素，C.sub.1-6烷氧基或C.sub.1-6烷基基团取代；Z是公式（d），（e）或（f）的基团：##STR2##其中n为2或3；p为1或2；q为1至3；r为1至3；R.sub.13和R.sub.14为C.sub.1-4烷基；具有5-HT.sub.3受体拮抗剂活性，其制备方法以及其作为药物的用途。
• Azabicyclic compounds, process for their preparation and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0289170A2

  公开（公告）日：1988-11-02

  Compounds of formula (I), or a pharmaceutically acceptable salt thereof:     Y-CO-L-Z      (I) wherein L      is NH or O; Y      is a group of formula (a), (b) or (c): wherein R₁ and R₂, R₅ and R₆, R₉ and R₁₀,      are independently selected from hydrogen or halogen; X      is N or CR₃ wherein R₃      is hydrogen or C₁₋₆ alkoxy; R₄      is hydrogen, halogen, CF₃, C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulphonyl, C₁₋₆ alkylsulphinyl, C₁₋₇ acyl, cyano, C₁₋₆ alkoxycarbonyl, C₁₋₇ acylamino, hydroxy, nitro or amino, aminocarbonyl, or aminosulphonyl, optionally N-substituted by one or two groups selected from C₁₋₆ alkyl, C₃₋₈ cycloalkyl, and C₃₋₈ cycloalkyl C₁₋₄ alkyl or disubstituted by C₄ or C₅ polymethylene; phenyl or phenyl C₁₋₄ alkyl group optionally substituted in the phenyl ring by one or two of halogen, C₁₋₆ alkoxy or C₁₋₆ alkyl groups;     one of R₇ and R₈      is C₁₋₆ alkyl and the other is C₁₋₆ alkyl, phenyl or phenyl C₁₋₄ alkyl optionally substituted in either phenyl ring by one or two of C₁₋₆ alkyl, C₁₋₆ alkoxy or halogen; or R₇ and R₈      together are C₂₋₆ polymethylene or C₂₋₅ polymethylene interrupted by an -O- linkage; R₁₁      is hydrogen or C₁₋₆ alkoxy; R₁₂      is hydrogen, halogen, CF₃, C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulphonyl, C₁₋₆ alkylsulphinyl, C₁₋₇ acyl, cyano, C₁₋₆ alkoxycarbonyl, C₁₋₇ acylamino, hydroxy, nitro or amino, aminocarbonyl, or aminosulphonyl, optionally N-substituted by one or two groups selected from C₁₋₆ alkyl, C₃₋₈ cycloalkyl, and C₃₋₈ cycloalkyl C₁₋₄ alkyl or disubstituted by C₄ or C₅ polymethylene; phenyl or phenyl C₁₋₄ alkyl optionally substituted in either phenyl ring by one or two of halogen, C₁₋₆ alkoxy or C₁₋₆ alkyl groups; Z      is a group of formula (d), (e) or (f): wherein n      is 2 or 3; p      is 1 or 2; q      is 1 to 3; r      is 1 to 3; and R₁₃ or R₁₄      is C₁₋₄ alkyl; having 5-HT₃ receptor antagonist activity, a process for their preparation and their use as pharmaceuticals.

  式 (I) 化合物或其药学上可接受的盐： Y-CO-L-Z (I) 其中 L 是 NH 或 O Y 是式 (a)、(b) 或 (c) 的基团： 其中 R₁ 和 R₂、R₅ 和 R₆、R₉ 和 R₁₀ 独立选自氢或卤素； X 是 N 或 CR₃ 其中 R₃ 是氢或 C₁₋₆ 烷氧基； R₄是氢、卤素、CF₃、C₁₋₆ 烷基、C₁₋₆ 烷氧基、C₁₋₆ 烷硫基、C₁₋₆ 烷基磺酰基、C₁₋₆ 烷基亚磺酰基、C₁₋₇酰基、氰基、C₁₋₆ 烷氧基羰基、C₁₋₇酰氨基、羟基、硝基或氨基、氨基甲酸乙酯、氨基甲酸乙酯、氨基甲酸乙酯、氨基甲酸乙酯、氨基甲酸乙酯、氨基甲酸乙酯、氨基甲酸乙酯、氨基甲酸乙酯、氨基甲酸乙酯硝基或氨基、氨基羰基或氨基磺酰基，可选择由一个或两个选自 C₁₋₆烷基的基团 N 取代、C₃₋₈ 环烷基和 C₃₋₈ 环烷基 C₁₋₄烷基或被 C₄ 或 C₅ 聚亚甲基二取代；苯基或苯基 C₁₋₄烷基，可选择在苯基环上被一个或两个卤素、C₁₋₆烷氧基或 C₁₋₆烷基取代； R₇ 和 R₈ 中的一个是 C₁₋₆ 烷基，另一个是 C₁₋₆ 烷基、苯基或 C₁₋₄烷基，可选择在任一苯基环上被一个或两个 C₁₋₆ 烷基、C₁₋₆ 烷氧基或卤素取代；或 R₇ 和 R₈ 合在一起是 C₂₋₆ 聚亚甲基或被 -O- 连接中断的 C₂₋₅ 聚亚甲基； R₁₁ 是氢或 C₁₋₆ 烷氧基； R₁₂是氢、卤素、CF₃、C₁₋₆ 烷基、C₁₋₆ 烷氧基、C₁₋₆ 烷硫基、C₁₋₆ 烷基磺酰基、C₁₋₆ 烷基亚磺酰基、C₁₋₇酰基、氰基、C₁₋₆ 烷氧羰基、C₁₋₇酰氨基、羟基、硝基或氨基、氨基甲酸乙酯、氨基甲酸乙酯、氨基甲酸乙酯、氨基甲酸乙酯、硝基或氨基、氨基羰基或氨基磺酰基，可选择由一个或两个选自 C₁₋₆烷基的基团 N 取代、C₃₋₈ 环烷基和 C₃₋₈ 环烷基 C₁₋₄烷基或被 C₄ 或 C₅ 聚亚甲基二取代；苯基或苯基 C₁₋₄烷基，可任选在任一苯基环上被一个或两个卤素、C₁₋₆烷氧基或 C₁₋₆烷基取代； Z 是式(d)、(e)或(f)的基团： 其中 n 是 2 或 3 p 是 1 或 2 q 是 1 至 3 r 为 1 至 3；以及 R₁₃ 或 R₁₄ 是 C₁₋₄ 烷基； 具有 5-HT₃ 受体拮抗剂活性，其制备方法及其作为药物的用途。